Oxidative Thiol Dimer Curing Agents for Tough Epoxy Adhesives

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Solution Overview

Problem

Existing epoxy resin compositions using sulfur compounds as curing agents suffer from unsatisfactory adhesive strength due to their flexible structure, and existing thiol compounds do not provide adequate toughness and workability in resin compositions.

Innovation Solution

A dimer of a specific trithiol compound, obtained by oxidative dimerization, is used as a curing agent in resin compositions, which includes an epoxy compound and optionally an ene compound with a carbon-carbon double bond, enhancing adhesive strength and workability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If sulfur compounds containing ether bonds are used as curing agents, then flexibility and moisture resistance are improved, but adhesive strength deteriorates due to structural flexibility

Engineering Contradiction:
Improveflexibility and moisture resistanceVSAvoidadhesive strength
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

The patent changes the molecular structure parameters of the curing agent by using thiol compounds with specific functional groups (mercapto groups) instead of sulfur compounds with ether bonds. This structural parameter change allows the curing agent to maintain crosslinking capability while reducing excessive flexibility, thereby improving adhesive strength without sacrificing moisture resistance

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite curing system by combining thiol compounds with epoxy resins and optionally incorporating silane-modified epoxy resins. This composite approach allows the thiol compound to provide crosslinking and the silane-modified epoxy to enhance adhesion to inorganic substrates, achieving both flexibility and adhesive strength simultaneously

Inventive Principle:
Principle #40Composite materials

2Speed

If conventional thiol compounds are used as curing agents, then cure rate is improved, but toughness and workability deteriorate

Engineering Contradiction:
Improvecure rateVSAvoidtoughness and workability
Core Design Contradiction:
SpeedVSStrength

Solution Approach 1:

The patent modifies the molecular weight and structure parameters of the thiol compound by selecting specific compounds with controlled molecular sizes. This parameter adjustment slows down the cure rate sufficiently to improve workability and toughness while maintaining adequate crosslink density for strength, resolving the contradiction between cure speed and mechanical properties

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces silane-modified epoxy resins as a localized modification within the curing system. This local quality enhancement provides specific adhesion properties and toughness without affecting the overall cure rate controlled by the thiol compound, allowing independent optimization of different performance aspects

Inventive Principle:
Principle #3Local quality

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The dimerized thiol compound improves the toughness and adhesive strength of cured resin products, providing improved workability and adhesive performance in resin compositions.

Implementation Method 1

a dimer obtained by oxidatively dimerizing a specific trithiol compound

Methodology Applied
Scientific EffectOxidative dimerization: Oxidation

Data Source

PatentUS20250289782A1Thiol compound and uses thereof
Publication Date: 2025.09.18 SHIKOKU CHEM CORP
  • US20250289782A1 patent drawing
  • US20250289782A1 patent drawing
  • US20250289782A1 patent drawing

AI summary

The present invention provides a novel thiol compound and use thereof. Specifically, the present invention provides a novel thiol compound, a curing agent containing the thiol compound, a resin composition containing the curing agent and an epoxy compound, a resin composition containing the curing agent and an ene compound having a carbon-carbon double bond in the molecule, and adhesives and sealants containing these resin compositions. The present invention relates to a dimer of a thiol compound represented by formula (II), a curing agent containing the dimer for resin, a resin composition containing the curing agent, an epoxy compound, and the like, and use of the resin composition.